Preheat the oven to 400 degrees F (205 degrees C). Line a baking sheet with parchment paper, aluminum foil, or a silicone baking mat.
Cut the Cauliflower (1/2 head) into 1-inch florets.
In a large bowl, toss together the cauliflower, Olive Oil (1 tablespoon), Salt (to taste), and Freshly Ground Black Pepper (to taste) until mixed.
Spread the cauliflower out on the baking sheet and roast for 25 minutes, or until the cauliflower just begins to brown. Halfway through the cooking time, stir the cauliflower so that it can brown evenly. Let cool for 10 minutes.
Once the cauliflower has cooled slightly, mix it with the Mayonnaise (1/3 cup), Yellow Mustard (1 tablespoon), and Dill Pickle Coins (1/4 cup) in a large bowl.
Sprinkle the Paprika (1 teaspoon) on top, then chill in the refrigerator for 3 hours before serving.